Reports directly to: Head of School

Department: Advancement

Position type: Full-time, 12-month contract

Location: Antilles School, 7280 Frenchman Bay, St. Thomas, VI 00802

Antilles School seeks a strategic and relationship-driven leader to serve as its Director of Advancement, a key member of the senior leadership team responsible for advancing philanthropic support, enrollment strategy, and institutional visibility.

Working in close partnership with the Head of School and Board of Trustees, the Director of Advancement develops and executes comprehensive strategies that strengthen philanthropy, support enrollment growth and retention, enhance community engagement, and elevate Antilles School’s visibility and reputation.

This role requires a visionary, results-oriented leader who brings strong relationship-building skills, strategic thinking, financial acumen, and a deep understanding of independent school culture and governance.

Core Responsibilities: 

The following responsibilities outline the essential functions of leadership and accountability for this role.

Strategic Leadership & Institutional Advancement

•  Develop and implement a comprehensive, data-informed advancement strategy aligned with the school’s strategic plan and long-term financial sustainability goals.
• Serve as a strategic advisor to the Head of School on matters related to fundraising, enrollment trends, donor engagement, institutional positioning, and community relations.
• Establish annual and multi-year advancement goals with measurable outcomes, including fundraising growth, donor retention, participation rates, and enrollment targets.
• Lead campaign planning and readiness efforts, including feasibility assessments and major gift strategy development.
• Partner closely with division leadership and administrative departments to align advancement efforts with school-wide priorities.

Fundraising & Philanthropy

• Oversee all aspects of the school’s philanthropic program, including Annual Fund, major gifts, capital and endowment initiatives, planned giving, and donor stewardship.
• Foster a strong culture of philanthropy across the school community.
• Personally manage and cultivate a portfolio of major gift prospects and donors.
• Partner with the Head of School in major gift strategy, donor solicitation, and stewardship efforts.
• Develop and implement donor recognition programs to strengthen long-term relationships and a culture of philanthropy.
• Oversee institutional grant strategy, including identification, proposal development, and stewardship of foundation and corporate funding opportunities.
• Ensure accurate donor reporting and compliance with ethical fundraising standards and best practices.

Enrollment & Revenue Strategy

•  Provide strategic oversight of the Admissions Office, ensuring enrollment goals align with the school’s financial and strategic objectives.
• Collaborate with the Chief Financial Officer to align tuition revenue forecasting, financial aid strategy, and enrollment modeling.
• Develop retention strategies in partnership with division leadership.
• Analyze enrollment and demographic data to inform recruitment and marketing strategies.

Marketing, Communications & Community Engagement

• Oversee school-wide marketing and communications strategies to ensure consistency in branding, storytelling, and institutional messaging.
• Strengthen the school’s visibility and reputation within the local and broader independent school community.
• Guide alumni engagement strategy and build meaningful, lifelong relationships with graduates and families.
• Support community engagement initiatives that enhance philanthropic and enrollment outcomes.
• Provide strategic oversight of advancement events and engagement activities to ensure alignment with fundraising and community-building goals.

Board Partnership & Governance

• Serve as staff liaison to the Board of Trustees’ Advancement Committee.
• Prepare and present advancement dashboards, enrollment reports, and campaign updates to the Board and its committees.
• Support the Head of School in managing board expectations related to fundraising and enrollment performance.
• Equip and support trustees and volunteer leaders in effective fundraising through training, coaching, and engagement strategies.

Leadership & Team Management

• Supervise and evaluate advancement, admissions, and communications personnel.
• Ensure alignment and accountability across advancement operations.
• Establish and maintain effective advancement operations, policies, and systems to ensure efficiency, compliance, and data integrity.
• Oversee the advancement budget and ensure responsible allocation of resources.
• Foster a collaborative, solutions-oriented culture within the Advancement team and across departments.

Qualifications:

• Bachelor’s degree required; Master’s degree in a relevant field preferred (education, nonprofit management, business administration, or related field).
• Minimum of seven years of progressive leadership experience in development, advancement, enrollment management, nonprofit leadership, or school administration.
• Demonstrated success in major gift fundraising, donor relations, and strategic planning.
• Proven track record of measurable fundraising growth and advancement program development.
• Strong understanding of enrollment management principles and tuition-driven financial models.
• Experience working effectively with boards of trustees and volunteer leadership preferred.
• Strong interpersonal and communication skills with the ability to engage effectively with diverse stakeholders, including trustees, donors, families, alumni, and community partners.
• Experience managing teams and leading cross-functional, collaborative projects.
• Financial literacy with the ability to interpret, analyze, and present data in a strategic and governance-level context.
• Familiarity with donor management software, CRM systems, and fundraising technology.
• Understanding of independent school culture and governance strongly preferred.
• High level of integrity, discretion, and professional judgment.
• Commitment to the mission, values, and culture of Antilles School.
• Demonstrated ability to lead in a mission-driven, relationship-centered independent school environment.

Additional Information: This is a full-time, 12-month administrative position requiring occasional travel and some evening and weekend commitments for school events and donor engagement. 

Antilles School is an Equal Opportunity Employer. We are committed to providing an inclusive and welcoming environment for all members of our community. Employment decisions are based on qualifications, merit, and school needs. Antilles School does not discriminate on the basis of race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status under federal, state, or local laws.

Applicants requiring reasonable accommodation for any part of the application process due to a disability may contact us at 340-776-1600 to request assistance. Information received related to accommodation will be treated confidentially.

This job posting is intended to convey information essential to understanding the scope of the position and is not intended to be an exhaustive list of duties, responsibilities, or qualifications. Antilles School reserves the right to modify job descriptions or job postings at any time, as business needs may dictate.